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Problem solving and design tasks are quite common across industries; as problems grow more complex and systems grow larger, design becomes increasingly a collaborative task. Design in itself already is challenging but collaboration adds its own challenges to the mix. In this paper, we explore the challenges of collaborative design. We approach the research question through design research framework as we synthesize the knowledge base and expert experiences to propositions about the challenges of collaborative design. We contribute to the discussion on collaborative design and we enable further research on how to support collaborative design activities.